Dimethyl acetylenedicarboxylate

Dimethyl acetylenedicarboxylate
Names
	Preferred IUPAC name Dimethyl but-2-ynedioate
	Other names DMAD; Acetylenedicarboxylic; acid dimethyl ester
Identifiers
CAS Number	762-42-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3248452;
ChemSpider	12440 ;
ECHA InfoCard	100.010.999
EC Number	212-098-4;
PubChem CID	12980;
RTECS number	ES0175000;
UNII	7HZA2PL15F;
CompTox Dashboard (EPA)	DTXSID0061088 ;
	InChI InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 Key: VHILMKFSCRWWIJ-UHFFFAOYSA-N ; InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 Key: VHILMKFSCRWWIJ-UHFFFAOYAX;
	SMILES COC(=O)C#CC(=O)OC;
Properties
Chemical formula	C6H6O4
Molar mass	142.11 g/mol
Appearance	Colorless liquid
Density	1.1564 g/cm3
Melting point	−18 °C (0 °F; 255 K)
Boiling point	195 to 198 °C (383 to 388 °F; 468 to 471 K) (96–98° at 8 mm Hg)
Solubility in water	Insoluble
Solubility in other solvents	Soluble in most; organic solvents
Refractive index (nD)	1.447
Structure
Dipole moment	0 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Flash point	187 °C (369 °F; 460 K)
Related compounds
Related compounds	Methyl propiolate,; Hexafluoro-2-butyne,; Acetylene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dimethyl acetylenedicarboxylate (DMAD) is an organic compound with the formula CH₃O₂CC₂CO₂CH₃. It is a di-ester in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly electrophilic, and is widely employed as a dienophile in cycloaddition reactions, such as the Diels-Alder reaction. It is also a potent Michael acceptor. This compound exists as a colorless liquid at room temperature. This compound was used in the preparation of nedocromil.

Names


Preferred IUPAC name Dimethyl but-2-ynedioate
Other names DMAD Acetylenedicarboxylic acid dimethyl ester
Identifiers
CAS Number	762-42-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3248452
ChemSpider	12440^Y
ECHA InfoCard	100.010.999
EC Number	212-098-4
PubChem CID	12980
RTECS number	ES0175000
UNII	7HZA2PL15F
CompTox Dashboard (EPA)	DTXSID0061088
InChI InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3^Y Key: VHILMKFSCRWWIJ-UHFFFAOYSA-N^Y InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 Key: VHILMKFSCRWWIJ-UHFFFAOYAX
SMILES COC(=O)C#CC(=O)OC
Properties
Chemical formula	C₆H₆O₄
Molar mass	142.11 g/mol
Appearance	Colorless liquid
Density	1.1564 g/cm³
Melting point	−18 °C (0 °F; 255 K)
Boiling point	195 to 198 °C (383 to 388 °F; 468 to 471 K) (96–98° at 8 mm Hg)
Solubility in water	Insoluble
Solubility in other solvents	Soluble in most organic solvents
Refractive index (n_D)	1.447
Structure
Dipole moment	0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Flash point	187 °C (369 °F; 460 K)
Related compounds
Related compounds	Methyl propiolate, Hexafluoro-2-butyne, Acetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references